Real Estate Investment Properties for Sale in Osterville, MA

Looking for investment property in Osterville, MA with high ROI ?

Explore a variety of short-term homes & houses in Osterville, MA. Invest wisely with VRBO & Osterville, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Osterville, MA

Search for Single Family Residential for Sale in Osterville, Massachusetts. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 29 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
168 Garrison Lane Osterville, MA Nestled amid beautifully landscaped grounds, this exceptional 7,500+/- square foot residen...	5 beds \| 6 baths \| 7,565 sq.ft.	$8,995,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -0.91% Airbnb Rental Income: $2096 Traditional Rental Income: $6857 Airbnb ROI: -1.54% Traditional ROI: -0.91%
162 Main Street Osterville, MA Fall in love the moment you step inside this beautifully renovated home that feels brand n...	3 beds \| 3 baths \| 2,048 sq.ft.	$1,785,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.61% Airbnb Rental Income: $1602 Traditional Rental Income: $3713 Airbnb ROI: -0.94% Traditional ROI: 0.61%
71 Sand Point Osterville, MA Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coasta...	5 beds \| 5 baths \| 5,747 sq.ft.	$12,250,000	Airbnb cash on cash: -1.78% Traditional cash on cash: -1.13% Airbnb Rental Income: $2096 Traditional Rental Income: $8910 Airbnb ROI: -1.78% Traditional ROI: -1.13%
14 Indian Trail Osterville, MA Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigiou...	5 beds \| 4 baths \| 3,087 sq.ft.	$9,850,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -0.86% Airbnb Rental Income: $2096 Traditional Rental Income: $6635 Airbnb ROI: -1.42% Traditional ROI: -0.86%
177 Bayview Circle Osterville, MA Summer is in the Air! Welcome 177 Bayview Circle and Osterville Village. Enjoy sunbathing ...	3 beds \| 3 baths \| 2,050 sq.ft.	$924,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.21% Airbnb Rental Income: $1602 Traditional Rental Income: $3330 Airbnb ROI: -0.32% Traditional ROI: 2.21%
280 Ice Valley Road Osterville, MA Set on an exceptionally oversized 2.94-acre corner parcel within Osterville's highly sough...	4 beds \| 6 baths \| 3,557 sq.ft.	$4,595,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 0.34% Airbnb Rental Income: $2167 Traditional Rental Income: $8486 Airbnb ROI: -1.27% Traditional ROI: 0.34%
351 Swift Avenue Osterville, MA Builder/Investor Opportunity in Osterville with Expansion Potential! Charming 3-bedroom, 1...	3 beds \| 1 baths \| 1,009 sq.ft.	$744,900	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.65% Airbnb Rental Income: $1602 Traditional Rental Income: $2414 Airbnb ROI: -0.18% Traditional ROI: 1.65%
5 Briar Patch Road Osterville, MA South of Route 28 in Osterville village, this inviting property offers an outstanding oppo...	3 beds \| 2 baths \| 1,497 sq.ft.	$875,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.28% Airbnb Rental Income: $1602 Traditional Rental Income: $3164 Airbnb ROI: -0.19% Traditional ROI: 2.28%
60 Linden Lane Osterville, MA Nestled in the heart of Osterville Village, this 3-bedroom, 3-bath home perfectly blends c...	3 beds \| 3 baths \| 2,000 sq.ft.	$949,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.53% Airbnb Rental Income: $1602 Traditional Rental Income: $3687 Airbnb ROI: -0.34% Traditional ROI: 2.53%
31 Falling Leaf Lane Osterville, MA This beautifully updated Osterville Cape, set on a private cul-de-sac, offers move-in-read...	3 beds \| 3 baths \| 2,190 sq.ft.	$1,199,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.61% Airbnb Rental Income: $1602 Traditional Rental Income: $3678 Airbnb ROI: -0.66% Traditional ROI: 1.61%
20 Deerfield Rd Osterville, MA Property is being offered via Real Estate Auction on Friday, June 26th at 11am on-site. Th...	3 beds \| 2 baths \| 2,076 sq.ft.	$874,400	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.99% Airbnb Rental Income: $1602 Traditional Rental Income: $3368 Airbnb ROI: 0.26% Traditional ROI: 2.99%
441 Old Mill Road Osterville, MA Osterville opportunity! Situated on 1.4 acres and abutting conservation land, this 2-bedro...	2 beds \| 2 baths \| 1,144 sq.ft.	$810,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.9% Airbnb Rental Income: $1218 Traditional Rental Income: $2702 Airbnb ROI: -0.58% Traditional ROI: 1.9%
21 Cockachoisett Lane Osterville, MA A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Cro...	4 beds \| 4 baths \| 3,015 sq.ft.	$2,900,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.32% Airbnb Rental Income: $2167 Traditional Rental Income: $5724 Airbnb ROI: -1.21% Traditional ROI: 0.32%
93 Oyster Way Osterville, MA Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal e...	4 beds \| 4 baths \| 4,964 sq.ft.	$4,795,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -0.52% Airbnb Rental Income: $2167 Traditional Rental Income: $5305 Airbnb ROI: -1.35% Traditional ROI: -0.52%
153 Hickory Hill Circle Osterville, MA This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect...	4 beds \| 3 baths \| 2,585 sq.ft.	$899,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.78% Airbnb Rental Income: $2167 Traditional Rental Income: $4506 Airbnb ROI: 0.33% Traditional ROI: 3.78%
170 Sturbridge Drive Osterville, MA Discover the charm and convenience of this lovingly maintained ranch-style home, perfectly...	2 beds \| 3 baths \| 1,992 sq.ft.	$1,150,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.28% Airbnb Rental Income: $1218 Traditional Rental Income: $3190 Airbnb ROI: -0.93% Traditional ROI: 1.28%
77 Robbins Street Osterville, MA Attention investors, second or year round home owners.. this perfectly located, updated, s...	4 beds \| 3 baths \| 2,976 sq.ft.	$1,349,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.88% Airbnb Rental Income: $2167 Traditional Rental Income: $4331 Airbnb ROI: -0.29% Traditional ROI: 1.88%
40 Waterfield Road Osterville, MA Your love affair will begin as you pull into the crushed stone, horseshoe drive w/ cobbles...	4 beds \| 2 baths \| 1,775 sq.ft.	$1,075,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.96% Airbnb Rental Income: $2167 Traditional Rental Income: $3553 Airbnb ROI: 0.03% Traditional ROI: 1.96%
33 Sunset Lane Osterville, MA A rare find in the village of Osterville! Discover a truly exceptional opportunity in the ...	3 beds \| 3 baths \| 1,686 sq.ft.	$1,599,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.39% Airbnb Rental Income: $1602 Traditional Rental Income: $3154 Airbnb ROI: -0.96% Traditional ROI: 0.39%
18 Winfield Lane Osterville, MA *OPEN HOUSE CANCELLED 4/4/26*Nestled near downtown Osterville with picturesque views a...	3 beds \| 3 baths \| 3,055 sq.ft.	$2,999,000	Airbnb cash on cash: -1.36% Traditional cash on cash: -0.36% Airbnb Rental Income: $1602 Traditional Rental Income: $3924 Airbnb ROI: -1.36% Traditional ROI: -0.36%
48 Bayview Circle Osterville, MA Nestled in Osterville Village, this charming Cape was completely remodeled in 20212 with a...	3 beds \| 3 baths \| 1,775 sq.ft.	$1,175,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.59% Airbnb Rental Income: $1602 Traditional Rental Income: $3499 Airbnb ROI: -0.56% Traditional ROI: 1.59%
82 Crystal Lake Road Osterville, MA Ideally situated for an easy walk to Osterville Village and Dowses beach, this home is per...	4 beds \| 4 baths \| 4,364 sq.ft.	$3,475,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 0.12% Airbnb Rental Income: $2167 Traditional Rental Income: $5566 Airbnb ROI: -1.1% Traditional ROI: 0.12%
176 Bumps River RD Osterville, MA Welcome to Osterville Living at Its Finest. Built in 2018 by the esteemed Barnstable Harbo...	3 beds \| 3 baths \| 2,537 sq.ft.	$1,495,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.33% Airbnb Rental Income: $1602 Traditional Rental Income: $4001 Airbnb ROI: -0.73% Traditional ROI: 1.33%
42 Oak Lane Osterville, MA Offered for the first time in generations, this lovely Cape Cod escape presents a rare opp...	3 beds \| 2 baths \| 1,848 sq.ft.	$849,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.36% Airbnb Rental Income: $1602 Traditional Rental Income: $3284 Airbnb ROI: -0.34% Traditional ROI: 2.36%

Your search for investment property begins and ends here

Single Family Homes for Sale in Osterville, MA

168 Garrison Lane

Osterville, MA

5 beds | 6 baths | 7,565 sq.ft.

$8,995,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: -0.91%

Airbnb Rental Income: $2096

Traditional Rental Income: $6857

Airbnb ROI: -1.54%

Traditional ROI: -0.91%

162 Main Street

Osterville, MA

3 beds | 3 baths | 2,048 sq.ft.

$1,785,000

Airbnb cash on cash: -0.94%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $1602

Traditional Rental Income: $3713

Airbnb ROI: -0.94%

Traditional ROI: 0.61%

71 Sand Point

Osterville, MA

5 beds | 5 baths | 5,747 sq.ft.

$12,250,000

Airbnb cash on cash: -1.78%

Traditional cash on cash: -1.13%

Airbnb Rental Income: $2096

Traditional Rental Income: $8910

Airbnb ROI: -1.78%

Traditional ROI: -1.13%

14 Indian Trail

Osterville, MA

5 beds | 4 baths | 3,087 sq.ft.

$9,850,000

Airbnb cash on cash: -1.42%

Traditional cash on cash: -0.86%

Airbnb Rental Income: $2096

Traditional Rental Income: $6635

Airbnb ROI: -1.42%

Traditional ROI: -0.86%

177 Bayview Circle

Osterville, MA

3 beds | 3 baths | 2,050 sq.ft.

$924,900

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1602

Traditional Rental Income: $3330

Airbnb ROI: -0.32%

Traditional ROI: 2.21%

280 Ice Valley Road

Osterville, MA

4 beds | 6 baths | 3,557 sq.ft.

$4,595,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $2167

Traditional Rental Income: $8486

Airbnb ROI: -1.27%

Traditional ROI: 0.34%

351 Swift Avenue

Osterville, MA

3 beds | 1 baths | 1,009 sq.ft.

$744,900

Airbnb cash on cash: -0.18%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $1602

Traditional Rental Income: $2414

Airbnb ROI: -0.18%

Traditional ROI: 1.65%

5 Briar Patch Road

Osterville, MA

3 beds | 2 baths | 1,497 sq.ft.

$875,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1602

Traditional Rental Income: $3164

Airbnb ROI: -0.19%